At 21-years-old, Trevor Jackson seems to have his life figured out. The Grown-ish star got a kickstart in acting as a child in 2004 when he earned the role of Simba in the Broadway staple The Lion King. At the time, he was only 8 years old but the experience would go on to be invaluable for Jackson who, today, claims that his theater experience shaped the rest of his life to follow.

Styled by Khalid Briggs

“That [experience] prepared me and inspired me to do that for the rest of my life,” Jackson tells Complex. “I moved to LA, recorded here and there, and then got signed when I was 15 years old to Atlantic. That kind of started my whole journey of being in studios, writing, working with different people, and then I started doing it on my own for this last album.”

Styled by Khalid Briggs

The album in question, Rough Drafts Pt. 1, is just one item in a long list of ventures that Jackson has been involved with recently. After a breakout guest spot on the critically acclaimed ABC series Black-ish, Jackson became a series regular on the show’s spin-off Grown-ish, as the hot-headed but relatable character Aaron Jackson (it is unclear whether producers named him that intentionally). Later this year, Jackson is set to star in a remake of the 1972 blaxploitation crime drama Super Fly.

With roles varying from a college undergraduate to an inner city crime boss, it seems like Jackson is accustomed to donning different hats depending on the day, and he claims this is also evident in his music and his style. “I’m spontaneous with my life. Monotony kills me, so I try and do everything differently every day just to get a different result and get something new out of life.”

Ask him about his style and he’d be the first to admit it’s rather happy-go-lucky. “It’s kind of hippy vibes a little bit...I like to not try too hard.” Jackson sees his onstage and offstage style as nearly one in the same. “Both [are] very relaxed, but on-stage, I try and do a little bit extra. Maybe more pops of color just so that the light catches it a little better.” While a fan of modern designs, it’s the ones that evoke a sense of nostalgia that resonate the most within Jackson. “I love vintage things. Anything out of the box, old school, and just different.”

Parsing the looks of Bloomingdale’s Spring Collection, the first look he pulls out is a certain floral jacket, a Hawaiian shirt, and matching pants. “I love that kind of thing. Anytime I think about Hawaii, I feel free.”

Styled by Khalid Briggs

Freedom seems to be at the forefront of Jackson’s art and is why he can rock a different style whenever he choses. On top of his varying roles, the songs on Rough Drafts play like a musical encyclopedia and aren’t tied to one specific genre. This is essential for Jackson. “You’ve got to love it and you’ve got to be comfortable,” Jackson maintains. “Try and be as free as possible to let the creative juices flow.”

Shop Trevor’s looks at Bloomingdale’s via links below:

First look:

Herschel Supply Co. Novel Duffle in Raven Cross Hatch $85.00

Ray-Ban Polarized Original Aviator Sunglasses, 58mm in Black $203.00

Calvin Klein Tricot Logo Track Jacket in White $98.00

Calvin Klein Logo Taped Tricot Track Pants in Black $89.50

Adidas Men’s Swift Run Sneakers in White $85.00

S’well Scarlet Bottle, 17 oz. $35.00

SOL ANGELES All A Dream Short Sleeve Tee in Heather $58.00

Makeup station:

MALIN and GOETZ Peppermint Shampoo 16 oz. $36.00

MALIN and GOETZ Cilantro Conditioner 8 oz. $24.00

MALIN and GOETZ Rum Body Lotion $35.00

Tom Ford Costa Azzurra Eau de Parfum 1.7 oz $230.00

Tom Ford Noir Anthracite Eau de Parfum 3.4 oz $171.00

Dior Sauvage Eau de Toilette 3.4 oz $95.00

Second look:

G-STAR RAW Motac Deconstructed 3D Cropped Slim Fit Jeans in White $190.00

Y-3 Leopard Mock Neck Short Sleeve Tee in White $130.00

Scotch & Soda Leaf Print Hooded Jacket in Black/Green $198.00

Adidas Men’s Campus Suede Lace Up Sneakers in Green $90.00